ArticleACS catalysis2019
Synthesis of α-Fluoro-α-Amino Acid Derivatives via Photoredox-Catalyzed Carbofluorination.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Manganese-Catalyzed Electrochemical Diazidation of Dehydroalanine Peptides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation.Beilstein journal of organic chemistry · 2024Article
- Iron-Catalyzed Synthesis of α-Azido α-Amino Esters via the Alkylazidation of Alkenes.Organic letters · 2023Article
- Stereoselective alkylChemical science · 2023Article
- Carbon-Centered Radicals in Protein Manipulation.ACS central science · 2023Review
- α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation.Angewandte Chemie (International ed. in English) · 2022Article
- carba-Nucleopeptides (cNPs): A Biopharmaceutical Modality Formed through Aqueous Rhodamine B Photoredox Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- Article
- Visible-light-mediated catalyst-free synthesis of unnatural α-amino acids and peptide macrocycles.Nature communications · 2021Article
- Combining flavin photocatalysis with parallel synthesis: a general platform to optimize peptides with non-proteinogenic amino acids.Chemical science · 2021Article
- Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CFAdvanced synthesis & catalysis · 2021Article
- Radical-Based Synthesis and Modification of Amino Acids.Angewandte Chemie (International ed. in English) · 2021Review
- Synthesis of complex unnatural fluorine-containing amino acids.Journal of fluorine chemistry · 2020Review
- Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.Chemical reviews · 2020Article
- Synthesis of Enantioenriched α-Deuterated α-Amino Acids Enabled by an Organophotocatalytic Radical Approach.Organic letters · 2020Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
A mild, metal-free, regioselective carbofluorination of dehydroalanine derivatives has been developed. Alkyl radicals resulting from visible-light photoredox catalysis engage in a radical conjugate addition to dehydroalanine, with subsequent fluorination of the newly generated radical to afford an α-fluoro-α-amino acid. By using a highly oxidizing organic photocatalyst, this process incorporates non-stabilized primary, secondary, and tertiary alkyl radicals derived from commercially available alkyltrifluoroborates to furnish a wide range of fluorinated unnatural amino acids.
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Registered trials
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